4-Chlorophenol → HCID 24776910, compound

HRID 2176970Notes

Reaction equation

HRID 2176970 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:18]=1[C:19]#[N:20]>CN(C)C=O.N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][C:17]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:18]=2[C:19]#[N:20])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 21928393HCID 21928393, compound

Product 1

HCID 24776910HCID 24776910, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Chlorophenol (64.0 mg; 0.5 mmol) and potassium carbonate were added to a cooled (0° C.) and stirred solution of 2-bromomethyl-6-nitrobenzonitrile (120.0 mg; 0.5 mmol) [prepared by the method of Ashton and Hynes, J. Med. Chem. 16, 1233 (1973)] in dimethylformamide under nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 1.5 hours, then diluted with pyridine (1.5 mL), water, stirred for 1 hour, filtered and dried to yield 140 milligrams of 2-(4-chlorophenoxymethyl)-6-nitrobenzonitrile.

Workup

  1. customprepared by the method of Ashton and Hynes, J
  2. stirringstirred for 1 hour
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-348577cdc7154fe19d794fa3d5b1bb3c
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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